#------------------------------------------------------------------------------
#$Date: 2020-06-04 03:55:52 +0300 (Thu, 04 Jun 2020) $
#$Revision: 252591 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/76/4517647.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4517647
loop_
_publ_author_name
'Matveevskaya, Vladislava V.'
'Pavlov, Dmitry I.'
'Sukhikh, Taisiya S.'
'Gushchin, Artem L.'
'Ivanov, Alexander Yu'
'Tennikova, Tatiana B.'
'Sharoyko, Vladimir V.'
'Baykov, Sergey V.'
'Benassi, Enrico'
'Potapov, Andrei S.'
_publ_section_title
;
 Arene-Ruthenium(II) Complexes Containing
 11H-Indeno[1,2-b]quinoxalin-11-one Derivatives and
 Tryptanthrin-6-oxime: Synthesis, Characterization, Cytotoxicity, and
 Catalytic Transfer Hydrogenation of Aryl Ketones.
;
_journal_issue                   19
_journal_name_full               'ACS omega'
_journal_page_first              11167
_journal_page_last               11179
_journal_paper_doi               10.1021/acsomega.0c01204
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C25 H22 Cl N3 O2 Ru'
_chemical_formula_sum            'C25 H22 Cl N3 O2 Ru'
_chemical_formula_weight         532.97
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-10-11
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.210(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.601(4)
_cell_length_b                   8.0342(18)
_cell_length_c                   17.108(4)
_cell_measurement_reflns_used    9774
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.73
_cell_measurement_theta_min      2.38
_cell_volume                     2141.0(9)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.734
_diffrn_reflns_theta_min         1.719
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0448 before and 0.0361 after correction. The Ratio of minimum to maximum transmission is 0.9410. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_description       prism
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         5550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0190
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0244P)²+1.0713P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5158
_reflns_number_total             5550
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c01204_si_003.cif
_cod_data_source_block           potru016
_cod_depositor_comments
'Adding full bibliography for 4517647--4517650.cif.'
_cod_original_cell_volume        2140.9(8)
_cod_database_code               4517647
_shelx_shelxl_version_number     2017/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.809
_shelx_estimated_absorpt_t_min   0.777
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ru1 Ru 0.80774(2) 0.53469(2) 0.41838(2) 0.02020(4) Uani 1 1 d . . . . .
Cl1 Cl 0.82682(3) 0.25336(5) 0.37474(2) 0.03802(9) Uani 1 1 d . . . . .
O1 O 0.87704(7) 0.44462(15) 0.57997(7) 0.0358(3) Uani 1 1 d . . . . .
O2 O 0.45816(8) 0.2368(2) 0.50512(8) 0.0554(4) Uani 1 1 d . . . . .
N1 N 0.81151(7) 0.44474(14) 0.53248(7) 0.0239(2) Uani 1 1 d . . . . .
N2 N 0.67604(7) 0.45772(15) 0.42718(7) 0.0243(2) Uani 1 1 d . . . . .
N3 N 0.59885(7) 0.31128(17) 0.52381(7) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.73736(9) 0.38514(18) 0.55443(8) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.66955(8) 0.38977(18) 0.49591(8) 0.0247(3) Uani 1 1 d . . . . .
C3 C 0.62048(10) 0.2565(2) 0.60187(8) 0.0307(3) Uani 1 1 d . . . . .
C4 C 0.57075(12) 0.1683(3) 0.65178(10) 0.0435(4) Uani 1 1 d . . . . .
H4 H 0.514779 0.136626 0.637215 0.052 Uiso 1 1 calc R . . . .
C5 C 0.60886(13) 0.1293(3) 0.72510(11) 0.0490(5) Uani 1 1 d . . . . .
H5 H 0.577479 0.069555 0.760277 0.059 Uiso 1 1 calc R . . . .
C6 C 0.69195(13) 0.1767(2) 0.74714(10) 0.0425(4) Uani 1 1 d . . . . .
H6 H 0.714925 0.149306 0.796810 0.051 Uiso 1 1 calc R . . . .
C7 C 0.74176(11) 0.2647(2) 0.69629(9) 0.0331(3) Uani 1 1 d . . . . .
H7 H 0.797582 0.296513 0.711307 0.040 Uiso 1 1 calc R . . . .
C8 C 0.70569(9) 0.30360(18) 0.62242(8) 0.0270(3) Uani 1 1 d . . . . .
C9 C 0.60334(9) 0.44466(18) 0.37590(8) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.60475(10) 0.5053(2) 0.29942(9) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.654695 0.552758 0.282202 0.039 Uiso 1 1 calc R . . . .
C11 C 0.53255(12) 0.4952(3) 0.24933(10) 0.0417(4) Uani 1 1 d . . . . .
H11 H 0.534151 0.536318 0.198612 0.050 Uiso 1 1 calc R . . . .
C12 C 0.45722(11) 0.4240(3) 0.27397(11) 0.0471(4) Uani 1 1 d . . . . .
H12 H 0.408542 0.419343 0.240091 0.056 Uiso 1 1 calc R . . . .
C13 C 0.45504(10) 0.3608(2) 0.34848(10) 0.0412(4) Uani 1 1 d . . . . .
H13 H 0.404973 0.311682 0.364518 0.049 Uiso 1 1 calc R . . . .
C14 C 0.52741(9) 0.3695(2) 0.40039(9) 0.0304(3) Uani 1 1 d . . . . .
C15 C 0.52142(9) 0.2989(2) 0.47920(9) 0.0339(3) Uani 1 1 d . . . . .
C16 C 0.84601(9) 0.78280(18) 0.46208(8) 0.0276(3) Uani 1 1 d . . . . .
C17 C 0.78287(10) 0.79876(18) 0.39966(9) 0.0297(3) Uani 1 1 d . . . . .
H17 H 0.731914 0.854350 0.408065 0.036 Uiso 1 1 calc R . . . .
C18 C 0.79606(9) 0.73115(18) 0.32425(8) 0.0290(3) Uani 1 1 d . . . . .
H18 H 0.755733 0.751527 0.283258 0.035 Uiso 1 1 calc R . . . .
C19 C 0.86810(9) 0.63516(19) 0.31067(8) 0.0290(3) Uani 1 1 d . . . . .
C20 C 0.93050(9) 0.6112(2) 0.37470(9) 0.0294(3) Uani 1 1 d . . . . .
H20 H 0.978072 0.544052 0.367872 0.035 Uiso 1 1 calc R . . . .
C21 C 0.92060(9) 0.68748(19) 0.44725(8) 0.0285(3) Uani 1 1 d . . . . .
H21 H 0.963657 0.675778 0.486708 0.034 Uiso 1 1 calc R . . . .
C22 C 0.83604(11) 0.8535(2) 0.54317(9) 0.0342(3) Uani 1 1 d . . . . .
H22 H 0.856083 0.768886 0.581202 0.041 Uiso 1 1 calc R . . . .
C23 C 0.74337(13) 0.8936(3) 0.55871(13) 0.0553(5) Uani 1 1 d . . . . .
H23A H 0.724337 0.986522 0.526998 0.083 Uiso 1 1 calc GR . . . .
H23B H 0.739272 0.920975 0.612993 0.083 Uiso 1 1 calc GR . . . .
H23C H 0.707926 0.798674 0.545942 0.083 Uiso 1 1 calc GR . . . .
C24 C 0.89393(15) 1.0058(3) 0.55512(12) 0.0511(5) Uani 1 1 d . . . . .
H24A H 0.952948 0.972079 0.554794 0.077 Uiso 1 1 calc GR . . . .
H24B H 0.883643 1.056885 0.604445 0.077 Uiso 1 1 calc GR . . . .
H24C H 0.881590 1.084093 0.513618 0.077 Uiso 1 1 calc GR . . . .
C25 C 0.87918(12) 0.5525(2) 0.23343(10) 0.0400(4) Uani 1 1 d . . . . .
H25A H 0.889759 0.435917 0.241490 0.060 Uiso 1 1 calc GR . . . .
H25B H 0.926930 0.601747 0.208941 0.060 Uiso 1 1 calc GR . . . .
H25C H 0.827972 0.566985 0.200340 0.060 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ru Ru -1.2594 0.8363 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ru1 Cl1 88.12(4) . . ?
N1 Ru1 N2 79.16(5) . . ?
N1 Ru1 C16 90.17(5) . . ?
N1 Ru1 C17 118.18(5) . . ?
N1 Ru1 C18 155.60(5) . . ?
N1 Ru1 C19 153.71(5) . . ?
N1 Ru1 C20 116.10(5) . . ?
N1 Ru1 C21 90.17(5) . . ?
N2 Ru1 Cl1 83.52(3) . . ?
N2 Ru1 C16 118.50(5) . . ?
N2 Ru1 C17 97.29(5) . . ?
N2 Ru1 C18 102.19(5) . . ?
N2 Ru1 C19 126.84(5) . . ?
N2 Ru1 C20 163.99(5) . . ?
N2 Ru1 C21 154.84(5) . . ?
C16 Ru1 Cl1 157.15(4) . . ?
C16 Ru1 C18 67.54(6) . . ?
C16 Ru1 C19 80.57(5) . . ?
C17 Ru1 Cl1 153.46(4) . . ?
C17 Ru1 C16 37.79(5) . . ?
C17 Ru1 C18 37.47(6) . . ?
C17 Ru1 C19 67.16(6) . . ?
C17 Ru1 C20 80.09(6) . . ?
C17 Ru1 C21 67.65(6) . . ?
C18 Ru1 Cl1 116.28(4) . . ?
C18 Ru1 C19 35.91(5) . . ?
C19 Ru1 Cl1 91.03(4) . . ?
C20 Ru1 Cl1 91.83(4) . . ?
C20 Ru1 C16 68.57(6) . . ?
C20 Ru1 C18 66.16(6) . . ?
C20 Ru1 C19 37.65(5) . . ?
C21 Ru1 Cl1 119.16(4) . . ?
C21 Ru1 C16 38.04(5) . . ?
C21 Ru1 C18 78.44(5) . . ?
C21 Ru1 C19 67.44(5) . . ?
C21 Ru1 C20 37.45(5) . . ?
O1 N1 Ru1 125.49(9) . . ?
O1 N1 C1 120.17(12) . . ?
C1 N1 Ru1 114.35(9) . . ?
C2 N2 Ru1 107.75(9) . . ?
C2 N2 C9 115.63(12) . . ?
C9 N2 Ru1 136.00(9) . . ?
C2 N3 C3 108.24(11) . . ?
C2 N3 C15 121.86(12) . . ?
C15 N3 C3 129.88(12) . . ?
N1 C1 C2 114.81(12) . . ?
N1 C1 C8 137.27(13) . . ?
C2 C1 C8 107.78(12) . . ?
N2 C2 N3 127.38(12) . . ?
N2 C2 C1 123.73(12) . . ?
N3 C2 C1 108.89(12) . . ?
C4 C3 N3 128.65(15) . . ?
C4 C3 C8 122.61(15) . . ?
C8 C3 N3 108.72(12) . . ?
C3 C4 C5 116.48(17) . . ?
C6 C5 C4 121.97(16) . . ?
C5 C6 C7 121.15(16) . . ?
C8 C7 C6 118.10(15) . . ?
C3 C8 C1 106.34(12) . . ?
C7 C8 C1 133.97(14) . . ?
C7 C8 C3 119.67(14) . . ?
N2 C9 C14 120.65(13) . . ?
C10 C9 N2 120.42(13) . . ?
C10 C9 C14 118.93(13) . . ?
C11 C10 C9 120.41(15) . . ?
C10 C11 C12 120.63(16) . . ?
C13 C12 C11 119.84(15) . . ?
C12 C13 C14 120.61(15) . . ?
C9 C14 C15 122.26(13) . . ?
C13 C14 C9 119.55(14) . . ?
C13 C14 C15 118.19(14) . . ?
O2 C15 N3 121.79(15) . . ?
O2 C15 C14 126.10(14) . . ?
N3 C15 C14 112.11(12) . . ?
C17 C16 Ru1 70.24(8) . . ?
C17 C16 C21 116.98(13) . . ?
C17 C16 C22 123.59(14) . . ?
C21 C16 Ru1 70.24(8) . . ?
C21 C16 C22 119.36(13) . . ?
C22 C16 Ru1 127.67(10) . . ?
C16 C17 Ru1 71.97(8) . . ?
C16 C17 C18 121.20(14) . . ?
C18 C17 Ru1 74.23(8) . . ?
C17 C18 Ru1 68.31(8) . . ?
C19 C18 Ru1 72.42(8) . . ?
C19 C18 C17 121.37(13) . . ?
C18 C19 Ru1 71.67(8) . . ?
C18 C19 C20 117.74(13) . . ?
C18 C19 C25 121.78(14) . . ?
C20 C19 Ru1 68.08(8) . . ?
C20 C19 C25 120.42(14) . . ?
C25 C19 Ru1 129.34(11) . . ?
C19 C20 Ru1 74.27(8) . . ?
C21 C20 Ru1 71.18(8) . . ?
C21 C20 C19 120.87(13) . . ?
C16 C21 Ru1 71.72(8) . . ?
C20 C21 Ru1 71.36(8) . . ?
C20 C21 C16 121.58(13) . . ?
C16 C22 C23 112.78(14) . . ?
C16 C22 C24 109.42(13) . . ?
C23 C22 C24 111.60(16) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ru1 Cl1 2.4042(6) . ?
Ru1 N1 2.0792(12) . ?
Ru1 N2 2.1589(12) . ?
Ru1 C16 2.1997(15) . ?
Ru1 C17 2.1772(15) . ?
Ru1 C18 2.2549(14) . ?
Ru1 C19 2.2646(14) . ?
Ru1 C20 2.1826(14) . ?
Ru1 C21 2.1803(14) . ?
O1 N1 1.2697(15) . ?
O2 C15 1.2119(19) . ?
N1 C1 1.3256(18) . ?
N2 C2 1.3054(18) . ?
N2 C9 1.3985(17) . ?
N3 C2 1.3787(17) . ?
N3 C3 1.4286(18) . ?
N3 C15 1.3958(18) . ?
C1 C2 1.4158(18) . ?
C1 C8 1.4459(19) . ?
C3 C4 1.381(2) . ?
C3 C8 1.408(2) . ?
C4 C5 1.394(3) . ?
C5 C6 1.383(3) . ?
C6 C7 1.391(2) . ?
C7 C8 1.390(2) . ?
C9 C10 1.397(2) . ?
C9 C14 1.414(2) . ?
C10 C11 1.379(2) . ?
C11 C12 1.393(3) . ?
C12 C13 1.374(3) . ?
C13 C14 1.399(2) . ?
C14 C15 1.470(2) . ?
C16 C17 1.417(2) . ?
C16 C21 1.428(2) . ?
C16 C22 1.515(2) . ?
C17 C18 1.425(2) . ?
C18 C19 1.393(2) . ?
C19 C20 1.437(2) . ?
C19 C25 1.497(2) . ?
C20 C21 1.401(2) . ?
C22 C23 1.519(3) . ?
C22 C24 1.528(2) . ?
